Anyway, thanks for fixing this.

It does work indeed!

Not sure if that is the complete fix - if you do something like:

with gpg.Context(...) as context:
    ...
... cause an exception after the context has been closed ...

then context will still be a valid reference to the gpg.Context instance, and may cause segfaults when something tries to access things inside it (f.e. for serialisation).
I like your previous solution with the accessor checks, because that actually fixes the issue.
Stylistically, maybe __del__ should just be renamed to cleanup or free, and then make sure to call that function from both __exit__ and __del__.

Can confirm, we've been running into this as well, but never filed a bug report. Our solution is to have this in our codebase:

Not exactly the answer I was hoping for..